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Classic Sailing in the Inner Hebrides

  • Vessel: Maybe
  • Where: Oban, Scotland
  • Duration: 6 days
  • Embark: Oban - 25 June 2023, 13:00
  • Disembark: Oban - 30 June 2023, 10:00
Single Berth in Twin Cabin£1,210.00 £302.50
Twin Cabin (single occupancy)£1,815.00 £453.75

Join tall ship Maybe for a Scottish sailing adventure to wild anchorages, sea lochs and quaint fishing ports in the Hebrides.

Your sailing adventure on classic boat Maybe begins in the bustling harbour town of Oban. Nestled in the West Coast of Scotland, Oban is a great place to begin your sailing holiday adventure into the Hebrides.

  • Fully Crewed Tall Ship
  • Island Hopping & Exploration
  • Wildlife Watching
  • Great for Couples or Solo Travellers
  • Private Cabins
  • Suitable for Beginners



Exploring the Hebrides by boat offers some of the most breath-taking and fascinating sailing grounds in the UK.  From remote anchorages where mountains run straight into the sea, miles of atmospheric landscapes, secret coves and uninhabited islands for walking trails ashore – sailing in the Hebrides certainly has something for everyone.

Exactly where you’ll discover will be at the whim of the wind and weather as with all our sailing holidays! The skipper and crew are familiar with the sailing area so know all the best spots to explore off the beaten track and spot the wondrous wildlife that the Hebrides has an abundance of.


Hebridean Sailing Highlights

Over 70 islands, both inhabited and uninhabited, make up the inner Hebrides so you won’t go short of any places to explore. Offering miles of coastline to explore and swathes of sea to sail, exploring this area by boat is the easiest and best way to see the Hebrides. The geography of the landscape also makes for great sailing conditions and shelter if the weather takes a turn.

The Isle of Mull is one of the larger inhabited islands in the Hebrides and is renowned for its abundance of wildlife. From dolphins, whales and sea eagles, endless walking trails and secluded anchorages, you could spend a week alone just exploring this beautiful island.

Iona sits just off the coast of Mull and its crystal clear, bright blue waters have made it one of our favourite spots in the inner Hebrides. It boasts ultimate tranquility, blue lagoons and sandy beaches only 1.5 x 3 miles!  Keep a look out  for oystercatchers, sandpipers, redshanks, plovers, curlews and greylag geese.

The Treshnish Isles

The Treshnish Isles are a small cluster of islands and skerries nestled off the West coast of Mull. An important area for marine animals and breeding seabirds, the islands are part of a Special Area of Conservation. The island of Lunga is home to a large puffin colony, where you can sit ashore within metres of the friendly faced creatures. The island of Staffa is home of the famous geological wonder of Fingal’s cave where guests can take the tender to get off and explore the impressive basalt columns.

Coll and Tiree

Tiree is known as the sunshine isle or ‘Hawaii of the North’ and boasts some of the highest recordings of sunshine in the UK with idyllic white sand beaches and turquoise water. Neighbouring Coll is more rugged with sandy coves and not a soul in sight. It is also known as a “dark sky park” as with no street light pollution, it has some of the darkest skies in Europe and is perfect for star watching.

Jura & Colonsay

If the winds are favourable to head South, you may find yourself sailing to explore the islands of Jura, Islay and Colonsay.

The Gulf of Corryvreckan lies between the islands and is home to the worlds third-largest whirlpool, Scarba which we will certainly say clear of! Jura, once the hideout for George Orwell to complete his famous 1984,  has only 200 inhabitants, massively outnumbered by its wild deer population which has been counted at approximately 5000.

The Isle of Colonsay is one of the smallest inhabited Hebridean islands and is known for its tranquillity and unspoilt natural beauty. Kiloran Bay is the most famous of many sandy beaches and crystal clear waters. From otters to seals to wild goats and a plethora of wild plants; Colonsay is rich in wild and unspoilt nature.


Sailing with classic boat Maybe is certainly an enjoyable, hands-on experience and guests are encouraged to get involved with all aspects of sailing this magnificent tall ship. From hoisting the sails to taking the helm, the friendly and knowledgable crew are always on hand to show you the ropes.

Maybe has a dedicated chef onboard too so you don’t have to worry about cooking after a days sailing in the salty sea air. Think locally sourced produce, fresh fish and home-made bread with hearty home-cooked meals and plenty of tea, coffee and cake! Your ticket price includes one glass of wine with your evening meal too.

If you’re new to sailing, don’t worry – the crew will guide you in exactly what to do, even if you’ve never stepped foot on a boat before. Sailing with Maybe is an experience you won’t forget! A beautifully restored classic tall ship, get involved with hoisting sails and being on hand to tack and jibe.

Read more about what to expect from a typical day and life onboard Maybe.

Your ticket price includes Breakfast, Lunch, Dinner and soft drinks. Bedding is provided – you just need to bring your own towels.

Similar voyages

VoyageSet SailDaysCost p/p
Classic Sailing in the Inner Hebrides18 June 20236£1,210.00Enquire now
Classic Sailing in the Inner Hebrides25 June 20236£1,210.00Enquire now

All voyages for Maybe

VoyageSet SailDaysCost p/p
Tall Ship Sailing in the Isles of Scilly5 July 20228£1,490.00Enquire now
Tall Ship Sailing in the Isles of Scilly14 July 20228£1,490.00Enquire now
Tall Ship sailing in the Isles of Scilly1 August 20227£1,323.00Enquire now
Cornish Coastal Sailing19 August 20227£1,323.00Enquire now
Tall Ship Sailing in Cornwall26 August 20224£662.00Enquire now
Cornish Coastal Sailing10 September 20225£882.00Enquire now
Tall Ship Sailing in Cornwall16 September 20224£662.00Enquire now
Sailing the Firth of Clyde27 May 20236£1,210.00Enquire now
Sailing the Firth of Clyde3 June 20236£1,210.00Enquire now
Sailing the Firth of Clyde & the Inner Hebrides10 June 20237£1,455.00Enquire now
Classic Sailing in the Inner Hebrides18 June 20236£1,210.00Enquire now
Classic Sailing in the Inner Hebrides25 June 20236£1,210.00Enquire now
Sailing the Inner Hebrides & the Firth of Clyde2 July 20237£1,455.00Enquire now
Sailing the Firth of Clyde & Southern Hebrides10 July 20236£1,210.00Enquire now
Taster Sailing the Firth of Clyde17 July 20234£695.00Enquire now
Tall Ship Sailing in the Isles of Scilly5 August 20237£1,455.00Enquire now
Tall Ship Sailing in the Isles of Scilly12 August 20237£1,455.00Enquire now
Tall Ship Sailing in the Isles of Scilly1 September 20238£1,630.00Enquire now
Tall Ship Sailing in the Isles of Scilly9 September 20238£1,630.00Enquire now
Tall Ship Taster Sailing in Cornwall22 September 20234£695.00Enquire now


Guest berths: 8 Rig: Gaff Ketch

Built in 1929, classic boat Maybe is a beautifully shaped 28m gaff ketch. A strong sea-worthy vessel, she is built with extra strength using steel frames, a hardwood hull and teak decking.

She has a rather famous history, once being owned by Jan Jacob Van Rietschoten, father of the flying Dutchman, Cornelis ‘Conny’ Van Rietschoten. Having spent most of her life privately owned sailing around the world, she has been owned by her present owners since 1989.

After a complete overhaul in 2007 and a restoration to her original Gaff rig in 2011, she now spends her summers sailing Cornwall and the Isles of Scilly and winters keeping warm in Spain and Portugal.

Guests are invited to get involved with all aspects of sailing Maybe, from hoisting the sails, taking the helm and even some basic navigation. An onboard chef provides breakfast, lunch, dinner, hot breads and cakes throughout voyages, ensuring you won’t be going hungry after a day on the water!

Read more about Life on board Maybe here.

More about Maybe


  • What COVID policies are in place for sailing with Maybe?

    There are currently no Test & Sail policies in place for the 2022 season.

  • Are all meals included?

    Yes, all meals on board are included in the price. (Breakfast, Lunch, Dinner and hot drinks) Generally, alcohol is not included; *One glass of wine is included with your evening meal on leisure voyages (not expedition/crossings)

  • Are bedding and towels provided?

    Bedding is provided. Please bring your own towels for swimming and showering

  • Can you cater for dietary needs?

    Yes, please let us know when making your booking.

  • What language is spoken onboard?


  • What are the sleeping arrangements?

    4x Twin Cabins(& 1x 6berth Cabin for private charters if needed)

  • Are bedding and towels included?

    All bedding is provided but towels are not so please bring your own for showering/swimming

  • Do I need to tip the crew?

    Tips are not mandatory but are welcomed by the crew!

  • How many toilet/showers does she have?

    2 toilets/showers for guest use

  • Is there WIFI?

    No, but you should easily be able to reach 3G/4G from the shore.

  • Can I charge my phone/Camera?


  • Are there life jackets provided?


  • Are Waterproofs provided?


  • Do I need sailing experience?

    No, absolutely not! Just a lust for adventure and a want to get actively involved.

  • Will I be sea sick?

    Everyone reacts differently but we recommend if you are at all worried to take some medication 24 hours before departure.

  • Is there an age limit?

    We recommend over 8+ years accompanied by an adult on a 1:1 ratio but please check in the office for any under 18's as it can vary from voyage to voyage.


From: Oban

To: Oban


There is ample parking in Oban if you arrive by car. Secure parking can be found at MacQueen Bros, or you could try the Tesco carpark and pay for 24 hour parking on arrival using the Your Parking Space app.


Oban station is a 5-10 minute walk from North Pier. Trains run 6 times a day to Glasgow Queen Street Station where there are good travel links to the rest of the UK.


Glasgow and Edinburgh Airport both require taking a train from Oban which takes approximately 2-3hours. Flights go direct to Stansted Airport.


There are plenty of places to stay in Oban. Try Witchwood House, The Scot or Perle Hotels Oban.

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